2-Methylbenzenesulfonamide → N-[1-(3-nitrobenzyl)indol-5-ylcarbonyl]-2-methylbenzene sulphonamide

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Reaction Steps

The carboxylic acid (Example 2) (6.2 g) was stirred at room temperature in dichloromethane (50 ml) with 2-methylbenzene sulphonamide (3.4 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (4.6 g) and 4-dimethylaminopyridine (0.25 g) for 72 hours. The reaction mixture was diluted with dichloromethane and washed with 0.5N hydrochloric acid, then water. The organic extract was dried over anhydrous magnesium sulphate, filtered and evaporated in vacuo. Purification by flash chromatography on silica, eluting with 0-2% ethyl acetate in dichloromethane, afforded N-[1-(3-nitrobenzyl)indol-5-ylcarbonyl]-2-methylbenzene sulphonamide (m.p. 208°-210° C.).

Provenance & Evidence